Methylecgonine cinnamate is a natural
tropane
Tropane is a nitrogenous Bicyclic molecule, bicyclic organic compound. It is mainly known for the other alkaloids derived from it, which include atropine and cocaine, among others. Tropane alkaloids occur in plants of the families Erythroxylaceae ...
alkaloid
Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar ...
found within the
coca
Coca is any of the four cultivated plants in the family Erythroxylaceae, native to western South America. Coca is known worldwide for its psychoactive alkaloid, cocaine.
The plant is grown as a cash crop in the Argentine Northwest, Bolivia, Al ...
plant. Its more common name, cinnamoylcocaine, reflects its close structural similarity to
cocaine
Cocaine (from , from , ultimately from Quechuan languages, Quechua: ''kúka'') is a central nervous system (CNS) stimulant mainly recreational drug use, used recreationally for its euphoria, euphoric effects. It is primarily obtained from t ...
. It is pharmacologically inactive,
[Merck Chemical Index, 1985] but some studies funded by anti-drug agencies imply that it is active when smoked. Furthermore, the discovery of differing impurity products yielding methylecgonine cinnamate in confiscated cocaine have led enforcing agencies to postulate that illicit manufacturers have changed their oxidation procedures when refining cocaine from a crude form. Methylecgonine cinnamate can dimerize to the
truxillic acid
Truxillic acids are any of several crystalline stereoisomeric cyclic dicarboxylic acids with the formula (C6H5C2H2(CO2H)2. They are colorless solids. These compounds are obtained by the + 2photocycloadditions of cinnamic acid where the two tra ...
derivative
In mathematics, the derivative of a function of a real variable measures the sensitivity to change of the function value (output value) with respect to a change in its argument (input value). Derivatives are a fundamental tool of calculus. F ...
truxilline.
It is notable that methylecgonine cinnamate is given in patents of active cocaine analogue structures.
U.S. patent US6479509 B1 structures given for submission, 5th compound down in image.
/ref>
See also
* Coca alkaloid
Coca alkaloids are the alkaloids found in the coca plant, ''Erythroxylum coca''.Variation of Alkaloid Content in Erythroxylum coca Leaves from Leaf Bud to Leaf Drop. Emanuel L. Johnson and Stephen D. Emche, Ann. Bot., 1994, volume 73, issue 6, page ...
s
* Cocaethylene
Cocaethylene (ethylbenzoylecgonine) is the ethyl ester of benzoylecgonine. It is structurally similar to cocaine, which is the methyl ester of benzoylecgonine. Cocaethylene is formed by the liver when cocaine and ethanol coexist in the blood. In ...
* Salicylmethylecgonine
Salicylmethylecgonine, (2′-Hydroxycocaine) is a tropane derivative drug which is both a synthetic analogue and a possible active metabolite of cocaine. Its potency ''in vitro'' is around 10x that of cocaine, although it is only around three t ...
References
External links
Isolation of ''cis''-Cinnamoylcocaine from Crude Illicit Cocaine via Alumina Column Chromatography
D.E.A.
The Drug Enforcement Administration (DEA; ) is a United States federal law enforcement agency under the U.S. Department of Justice tasked with combating drug trafficking and distribution within the U.S. It is the lead agency for domestic enf ...
Microgram Vol 4 Number 14.
*{{cite journal , year = 2015 , title = Possibilities for discrimination between chewing of coca leaves and abuse of cocaine by hair analysis including hygrine, cuscohygrine, cinnamoylcocaine and cocaine metabolite/cocaine ratios , journal = International Journal of Legal Medicine , volume = 129 , issue = 1, pages = 69–84 , doi=10.1007/s00414-014-1061-6, pmid = 25138383 , last1 = Rubio , first1 = Nelida Cristina , last2 = Hastedt , first2 = Martin , last3 = Gonzalez , first3 = Jorge , last4 = Pragst , first4 = Fritz , s2cid = 20712368
Tropane alkaloids found in Erythroxylum coca
Cinnamate esters
Methyl esters